頻那醇硼烷
外觀
頻那醇硼烷 | |
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IUPAC名 4,4,5,5-Tetramethyl-1,3,2-dioxaborolane | |
別名 | HBpin |
識別 | |
CAS號 | 25015-63-8 |
PubChem | 6364989 |
ChemSpider | 2016512 |
SMILES |
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性質 | |
化學式 | C6H13BO2 |
摩爾質量 | 127.98 g·mol−1 |
外觀 | colorless liquid |
密度 | 0.882 g/cm3 |
沸點 | 42-43 °C(272 K) |
危險性 | |
GHS危險性符號![]() ![]() ![]() | |
GHS提示詞 | Danger |
H-術語 | H220, H225, H260, H261, H315, H318 |
P-術語 | P210, P223, P231+232, P233, P240, P241, P242, P243, P264, P280, P302+352, P303+361+353, P305+351+338, P310 |
若非註明,所有數據均出自標準狀態(25 ℃,100 kPa)下。 |
頻那醇硼烷的結構簡式為(CH3)4C2O2BH。 此硼烷的一個重要特點為,它有一個含硼原子的五元環C2O2B。 在含硼烷氧基化合物這一類分子中, 頻那醇硼烷為單體。 它是無色液體,溶於醚、四氫呋喃以及二氯甲烷等有機溶劑中。[1] 其反應性很強的B-H基團常被用在有機化學反應中。[2]
在有機合成中的應用
[編輯]頻那醇硼烷被用於將烯烴、炔烴硼氫化,炔烴的硼氫化反應相對較慢。上述反應需要催化劑的存在。[2][3]
頻那醇硼烷也被用在醛[4]、酮[5]以及羧酸[6]的無催化劑硼氫化反應中。
頻那醇硼烷也被用於將有機化合物的C-H鍵硼化,這類反應屬於碳氫鍵活化.[7][8]
頻那醇硼烷的雙分子脫氫反應可以生成雙頻那醇硼烷(B2pin2):[9]
- 2 (CH3)4C2O2BH → (CH3)4C2O2B-BO2C2(CH3)4 + H2
相關物質
[編輯]參考文獻
[編輯]- ^ Ramachandran, P. Veeraraghavan; Chandra, J. Subash; Ros, Abel; Fernández, Rosario; Lassaletta, José M.; Aggarwal, Varinder K.; Blair, Daniel J. Encyclopedia of Reagents for Organic Synthesis: 1–12. 2017. ISBN 9780470842898. doi:10.1002/047084289X.rn00574.pub3.
|chapter=
被忽略 (幫助) - ^ 2.0 2.1 Brown, H.C.; Zaidlewicz, M. Organic Syntheses Via Boranes, Vol. 2. Milwaukee, WI: Aldrich Chemical Co. 2001. ISBN 978-0-9708441-0-1.
- ^ Ely, Robert J.; Morken, James P. Stereoselective Nickel-Catalyzed 1,4-Hydroboration of 1,3-Dienes. Organic Syntheses. 2011, 88: 342. doi:10.15227/orgsyn.088.0342
.
- ^ Stachowiak, Hanna; Kaźmierczak, Joanna; Kuciński, Krzysztof; Hreczycho, Grzegorz. Catalyst-free and solvent-free hydroboration of aldehydes. Green Chemistry. 2018, 20 (8): 1738–1742. ISSN 1463-9262. doi:10.1039/C8GC00042E (英語).
- ^ Wang, Weifan; Luo, Man; Yao, Weiwei; Ma, Mengtao; Pullarkat, Sumod A.; Xu, Li; Leung, Pak-Hing. Catalyst-free and solvent-free hydroboration of ketones. New Journal of Chemistry. 2019, 43 (27): 10744–10749. ISSN 1144-0546. doi:10.1039/C9NJ02722J (英語).
- ^ Harinath, Adimulam; Bhattacharjee, Jayeeta; Panda, Tarun K. Facile Reduction of carboxylic acids to primary alcohols under catalyst-free and solvent-free conditions. Chemical Communications. 2019, 55 (10): 1386–1389. ISSN 1359-7345. PMID 30607398. doi:10.1039/C8CC08841A (英語).
- ^ Amaike, K.; Loach, R. P.; Movassaghi, M. Direct C7 Functionalization of Tryptophan. Synthesis of Methyl (S)-2-((tert-Butoxycarbonyl)amino)-3-(7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indol-3-yl)propanoate. Organic Syntheses. 2015, 92: 373–385. PMC 4733874
. PMID 26839440. doi:10.15227/orgsyn.092.0373 (不活躍 31 May 2021).
- ^ Ishiyama, Tatsuo; Takagi, Jun; Nobuta, Yusuke; Miyaura, Norio. Iridium-Catalyzed C-H Borylation of Arenes and Heteroarenes: 1-Chloro-3-Iodo-5-(4,4,5,5-Tetramethyl-1,3,2-Dioxaborolan-2-Yl)Benzene and 2-(4,4,5,5,-Tetramethyl-1,3,2-Dioxaborolan-2-Yl)Indole. Organic Syntheses. 2005, 82: 126. doi:10.15227/orgsyn.082.0126. hdl:2115/56319
.
- ^ Neeve, Emily C.; Geier, Stephen J.; Mkhalid, Ibraheem A. I.; Westcott, Stephen A.; Marder, Todd B. Diboron(4) Compounds: From Structural Curiosity to Synthetic Workhorse. Chemical Reviews. 2016, 116 (16): 9091–9161. PMID 27434758. doi:10.1021/acs.chemrev.6b00193
.